Phenylpyrazole insecticides

Chemical structure of fipronil, a common phenylpyrazole insecticide

Phenylpyrazole insecticides are a class of chemically-related broad-spectrum insecticides.^[1] The chemical structures of these insecticides are characterized by a central pyrazole ring with a phenyl group attached to one of the nitrogen atoms of the pyrazole.

History

Phenylpyrazole insecticides were developed in response to increasing pesticide resistance to other chemicals. Now, along with neonicotinoids, they are some of the most widely-used pesticides.^[1]

Mode of Action

Phenylpyrazole insecticides function by blocking GABA-gated chloride channels in insects (IRAC group 2B).^[1] Mammals do not have this type of chloride channel, making them much less susceptible to its effects. However, they do have the capacity to disrupt epithelial cells in the human intestine and adversely impact human health.^[2]

Examples

Examples include:

acetoprole
ethiprole
fipronil
flufiprole
pyraclofos
pyrafluprole
pyriprole
pyrolan
vaniliprole

References

^ ^a ^b ^c Jeschke, Peter; Witschel, Matthias; Krämer, Wolfgang; Schirmer, Ulrich (25 January 2019). "33.5 GABA‐gated Chloride Channel Antagonists (Fiproles)". Modern Crop Protection Compounds (3rd ed.). Wiley‐VCH. pp. 1449–1478. ISBN 9783527699261.{{cite book}}: CS1 maint: date and year (link)
^ Vidau, C.; Brunet, J. L.; Badiou, A.; Belzunces, L. P. (2009). "Phenylpyrazole insecticides induce cytotoxicity by altering mechanisms involved in cellular energy supply in the human epithelial cell model Caco-2". Toxicology in Vitro. 23 (4): 589–597. doi:10.1016/j.tiv.2009.01.017.

External links

Media related to phenylpyrazole insecticides at Wikimedia Commons

[:0-1] Jeschke, Peter; Witschel, Matthias; Krämer, Wolfgang; Schirmer, Ulrich (25 January 2019). "33.5 GABA‐gated Chloride Channel Antagonists (Fiproles)". Modern Crop Protection Compounds (3rd ed.). Wiley‐VCH. pp. 1449–1478. ISBN 9783527699261.{{cite book}}: CS1 maint: date and year (link)

[Vidau_2009-2] Vidau, C.; Brunet, J. L.; Badiou, A.; Belzunces, L. P. (2009). "Phenylpyrazole insecticides induce cytotoxicity by altering mechanisms involved in cellular energy supply in the human epithelial cell model Caco-2". Toxicology in Vitro. 23 (4): 589–597. doi:10.1016/j.tiv.2009.01.017.

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